Braced frames are a common lateral force-resisting system in mass timber structures. In timber braced frames, timber-steel dowel connections are relied upon to provide ductility and energy dissipation capacity under earthquake loads. However, the ductility and energy dissipation capacity of these connections can be limited by the onset of a brittle failure mechanism (e.g., row-shear or group tear-out) prior to significant dowel yielding. This paper presents an experimental campaign investigating the structural performance of timber-steel dowelled connections reinforced with self-tapping screws. Twelve connections were tested; with 8 tested under monotonic loading and 4 tested under a cyclic loading regime. The tested connections included two different fastener diameters of 11 mm and 16 mm, with one or two internal steel plates, both with and without reinforcing screws designed to prevent brittle shear failure. The results demonstrate that the reinforcing screws are most effective for improving the ductility and energy dissipation for connections with similar design values of dowel yield and row shear capacities. In addition, the increases in ductility and energy dissipation with reinforcement were greatest for connections with high slenderness (defined as the ratio of dowel diameter to timber thickness) dowels. There was little improvement in the ductility of connections whose design capacity was dominated by row shear, although there was improvement in the energy dissipation of the connections. Overall, results of this study demonstrate the potential for using self-tapping screws to reinforce steel dowel connections and improve the seismic performance of mass timber braced frames.